Comedy Legend Dies
Comedy Pioneer Tom Dreesen, known for interracial duo and opening for Sinatra, dies at 86
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Tom Dreesen, the comedian who helped form the first interracial stand-up duo in U.S. history and spent 13 years opening for Frank Sinatra, died on June 18, 2026, at age 86 in Los Angeles. His publicist Rick Miramontez confirmed the news, saying Dreesen "died peacefully surrounded by family" following a brief illness, according to Associated Press.
Dreesen rose from extreme poverty in Harvey, Illinois — shining shoes and setting bowling pins as a boy — to performing for millions worldwide alongside the greatest entertainer of the 20th century. His death closes one of the last direct links to the Frank Sinatra era.
The Interracial Duo That Made History in 1969
While working at an insurance office, Dreesen met Tim Reid through a local Jaycees chapter. The two formed "Tim and Tom" in 1969 — the first interracial stand-up comedy duo in American history, according to The Hollywood Reporter. They launched their act just one year after the assassination of Dr. Martin Luther King Jr., when an interracial pair sharing a stage was itself a political act.
The duo toured the Chitlin' Circuit and mainstream clubs alike, often facing threats of violence in the Deep South and being forced to stay in separate hotels. They disbanded amicably in 1973. In 2008, Dreesen and Reid co-wrote "Tim & Tom: An American Comedy in Black and White," published by the University of Chicago Press. Reid called Dreesen "my brother in every way that counts," adding: "We didn't just break a color barrier; we learned how to be human beings together in a world that didn't always want us to."
Thirteen Years Opening for Old Blue Eyes
After moving to Los Angeles in the early 1970s with nothing in his pocket, Dreesen built a solo career at The Comedy Store. He made his debut on "The Tonight Show Starring Johnny Carson" in 1975. Then in 1982, Frank Sinatra heard his act and invited him to open a show in Halifax. That single night turned into a 13-year partnership, according to Associated Press.
Dreesen performed in more than 500 cities alongside Sinatra until the singer's retirement in 1995. He was one of the few people permitted to speak at Sinatra's funeral in 1998. Comedy historian Mark Evanier told Variety: "You didn't feel like Sinatra was closing for him — you felt like Sinatra was closing for him." Dreesen appeared on David Letterman's programs more than 61 times over his career.
A Harvey, Illinois Kid Who Never Forgot Home
Dreesen grew up in grinding poverty in Harvey, a blue-collar suburb south of Chicago. He shined shoes and set pins in bowling alleys as a child to help support his family. That hard upbringing, he often said, gave him the grit to handle hostile crowds in the 1970s. The Mayor of Chicago issued a statement saying Dreesen "never forgot where he came from," highlighting his charity work for the MS Society and his hometown.
Local Chicago outlets framed his story as a classic pull-yourself-up tale — the shoeshine boy who opened for the Chairman of the Board. National outlets focused more on his role as a Civil Rights-era trailblazer. Entertainment press zeroed in on the Sinatra glamour years: the private jets, the Vegas nights, the Rat Pack orbit. All three readings are true at once.
What Dreesen's Death Means for Comedy's Lost Art
Dreesen was one of the last working performers with a direct firsthand memory of touring with Sinatra. His "Sinatra Stories" — told in interviews and on stage — are considered the clearest window into the singer's final touring years. Experts say his passing may spark renewed interest in his archives and a possible documentary on the "Tim and Tom" years, according to Variety.
Dreesen championed what he called "clean" comedy — jokes that worked in any room, for any crowd. In an era built around solo streaming specials and niche audiences, his career was a reminder that the opening act was once its own art form. He mastered it better than almost anyone.
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